Dyestuffs of the anthraquinone series



Patented May 2, 1939 UNITED STATES PATENT OFFICE DYESTUFFS OF THE; ANTHRAQUINONE SERIES Claus Weinand, Leverkusen I. G. Work, Germany, assignor to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application September 15, 1936, Serial No. 100,874. In Germany September 21, 1935 3 Claims. (Cl. 260-374) The present invention relates to new dyestuffs cooling the condensation product precipitates of the anthraquinone series and to a process and is isolated in the usual manner. of preparing same.

The new dyestuffs which are obtainable in Fmmple 2 accordance with my present invention are the 20 Parts P 1-am1n0-4-b10m0aHUhFaQHiIIOHE-Z- 5 products of the interaction of 2 mols of a Sulfonic acld are heated to bo in lamino 4 halogenanthraquinone 2 sulfonic 300 parts of water and acld Wlth of an lP S1ected from the 100 parts of methylalcohol in admixture with group consist ng of diaminodiphenylmethanes 20 parts of pap, djammodiphenylcyclohexane' and d1aminotriphenylmethanes. Preferably such 20 parts of Soda and diaminodiphenylmethanes are employed wherein 1 part of copper sulfate the amino groups are in p,p-pos1t1on; the hydrogen atoms f the methane carbon atom may until the first yellow-red solution has turned be substituted by alkyl radicals, such as methyl 9 Durmg the reactjwn the fiiyestufi groups Among the diammotriphenylmethanes precipitates in blue needles WhlCh are isolated 15 likewise those compounds are preferred which 1n the usual mannercontain the amino groups in p,p'-positions. Example 3 The new dyestuffs are soluble in water with a 40 t f 1 4 b th 2 blue to bluish-green coloration and dye wool S .raqumone' from an acid bath blue to bluish-green shades. sulfomc are heated to boflmg m 20 They are distinguished by their excellent fast- 400 parts of water and ness properties, particularly towards acids. 100 parts of ethylalcohol in admixture with My new dyestufis can be prepared by causing 10 parts of p,p-diaminodiphenyldimethylmeth- 2 mols of a 1-amino-4-halogenanthraquinone-2 ane, sulfonic acid, preferably of the bromo compound, 40 parts of soda and 25 to react upon 1 mol of a diamino compound of 3 parts of cuprous chloride the character described The reaction must be until the solution has turned dark blue. When performed in an aqueous alcoholic medium as cooling the dyestuff precipitates in blue needles, otherwise only 1 mol of the 1-amino-4-halogenwhich are isolated in the usual ma en 30 starter; tz tzttstsm zttit If 1o f p methylmethane are substituted by 12 parts of binding agents I preferably add sodium carbondi t h 1 th d i ate or sodium bicarbonate. The addition of amu-lo up me ane yes 0 Sumlar shades is obtained. catalysts, such as of a cupric or cuprous salt I claim, ggg' f an accelerating actmn upon the 1. The product of the reaction of 2 mols of a 35 The following examples illustrate the inven- 3 23?' f' l fi tion the parts being by weight: a 1 O lammo 1p (my me ane in which both hydrogen atoms of the V methanecarbon atom are substituted by a radical Example 1 selected from the group consisting of alkyl and 20 parts of 1 ammo; bromoanthmqumone alkylene, said alkylene radicals being joined to 2-sulfonic acid are heated to boiling while reform a slx'membered fluxing in 2. The product of the reaction of 2 mols of a 5 l-amino 4 halogenanthraquinone 2- sulfonic 300 parts of water and acid and 1 mol of p,p-diaminodiphenyldimethylparts or ethylalcohol in admixture with methane- 20 parts of p,p'-diaminodiphenylmethane, 3. The product of the reaction of 2 mols of a 10 parts of soda and l-amino 4 halogenanthraquinone 2 sulfonic 5o 1 t of cuprous bromide, 1alcid and 1 mol of p,p'-diaminodiphenylcyclow exane.

The solution quickly turns dark blue. 'When CLAUS WEINAND. 

